posted on 2000-02-09, 00:00authored byMichael Pete VanBrunt, Robert F. Standaert
Furanomycin is a Streptomyces metabolite that substitutes for isoleucine in protein translation. We report a concise and modular synthesis
starting from the Garner aldehyde and proceeding in seven steps to furanomycin. The key steps include a stereoselective acetylide addition
and the Ag+-mediated cyclization of an α-allenic alcohol to construct the trans-2,5-dihydrofuran. The efficiency (12% overall yield) and flexibility
of the route will provide ample quantities of furanomycin and analogues for protein engineering.